SK1032001A3 - Alpha-amino acid phenyl ester derivatives - Google Patents

Alpha-amino acid phenyl ester derivatives Download PDF

Info

Publication number: SK1032001A3
Authority: SK; Slovakia
Prior art keywords: acid; amino; amino acid; alkyl; dimethoxyphenyl
Prior art date: 1998-07-22

Application number

SK103-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Niall Morton Hamilton

Original Assignee

Akzo Nobel Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-07-22

Filing date

1999-07-16

Publication date

2001-08-06

1999-07-16 Application filed by Akzo Nobel Nv filed Critical Akzo Nobel Nv

2001-08-06 Publication of SK1032001A3 publication Critical patent/SK1032001A3/sk

Links

-1 Alpha-amino acid phenyl ester Chemical class 0.000 title claims abstract description 99
235000008206 alpha-amino acids Nutrition 0.000 title claims abstract description 26
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 18
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
230000000147 hypnotic effect Effects 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 45
KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 14
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
229960003692 gamma aminobutyric acid Drugs 0.000 claims description 7
150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
208000019901 Anxiety disease Diseases 0.000 claims description 2
206010010904 Convulsion Diseases 0.000 claims description 2
201000009916 Postpartum depression Diseases 0.000 claims description 2
206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
230000036506 anxiety Effects 0.000 claims description 2
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
201000000484 premenstrual tension Diseases 0.000 claims description 2
239000000932 sedative agent Substances 0.000 claims description 2
230000000202 analgesic effect Effects 0.000 claims 1
230000001624 sedative effect Effects 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
239000003326 hypnotic agent Substances 0.000 abstract description 5
206010002091 Anaesthesia Diseases 0.000 abstract description 3
230000037005 anaesthesia Effects 0.000 abstract description 3
230000006698 induction Effects 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
238000001949 anaesthesia Methods 0.000 abstract 1
238000012423 maintenance Methods 0.000 abstract 1
238000005481 NMR spectroscopy Methods 0.000 description 61
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 61
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
150000002500 ions Chemical class 0.000 description 25
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 12
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000007787 solid Substances 0.000 description 10
IHMGFZLHMQPGRB-UHFFFAOYSA-N (2,6-dimethoxyphenyl) butanoate Chemical compound CCCC(=O)OC1=C(OC)C=CC=C1OC IHMGFZLHMQPGRB-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
QRPQVVRHSVAUCY-UHFFFAOYSA-N (2,6-dimethoxy-4-methylphenyl) butanoate Chemical compound CCCC(=O)OC1=C(OC)C=C(C=C1OC)C QRPQVVRHSVAUCY-UHFFFAOYSA-N 0.000 description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002253 acid Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
UOAAWEZUMVNYAT-UHFFFAOYSA-N (2,6-dimethoxyphenyl) propanoate Chemical compound CCC(=O)OC1=C(OC)C=CC=C1OC UOAAWEZUMVNYAT-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000001990 intravenous administration Methods 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
238000000034 method Methods 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000011734 sodium Substances 0.000 description 5
PASDZKDXDGIFPU-UHFFFAOYSA-N (2,6-dimethoxy-4-methylphenyl) propanoate Chemical compound CCC(=O)OC1=C(OC)C=C(C)C=C1OC PASDZKDXDGIFPU-UHFFFAOYSA-N 0.000 description 4
ZFBNNSOJNZBLLS-UHFFFAOYSA-N 2,6-Dimethoxy-4-methylphenol Chemical compound COC1=CC(C)=CC(OC)=C1O ZFBNNSOJNZBLLS-UHFFFAOYSA-N 0.000 description 4
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
VTBHBNXGFPTBJL-UHFFFAOYSA-N 4-tert-butyl-1-sulfanylidene-2,6,7-trioxa-1$l^{5}-phosphabicyclo[2.2.2]octane Chemical compound C1OP2(=S)OCC1(C(C)(C)C)CO2 VTBHBNXGFPTBJL-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000003193 general anesthetic agent Substances 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
GWNIEAJQMCBQHC-UHFFFAOYSA-N (2,6-dimethoxy-4-methylphenyl) 2-bromobutanoate Chemical compound CCC(Br)C(=O)OC1=C(OC)C=C(C)C=C1OC GWNIEAJQMCBQHC-UHFFFAOYSA-N 0.000 description 2
MCTFQDODOWYOIR-UHFFFAOYSA-N (2,6-dimethoxy-4-methylphenyl) 2-bromohexanoate Chemical compound CCCCC(Br)C(=O)OC1=C(OC)C=C(C)C=C1OC MCTFQDODOWYOIR-UHFFFAOYSA-N 0.000 description 2
QCQWVVNWUYVAGV-UHFFFAOYSA-N (2,6-dimethoxyphenyl) 2-morpholin-4-ylpropanoate Chemical compound COC1=CC=CC(OC)=C1OC(=O)C(C)N1CCOCC1 QCQWVVNWUYVAGV-UHFFFAOYSA-N 0.000 description 2
NNFDHJQLIFECSR-UHFFFAOYSA-N 2-bromo-4-methylpentanoic acid Chemical compound CC(C)CC(Br)C(O)=O NNFDHJQLIFECSR-UHFFFAOYSA-N 0.000 description 2
IQGRVWSONWFJJD-UHFFFAOYSA-N 2-bromo-4-methylpentanoyl chloride Chemical compound CC(C)CC(Br)C(Cl)=O IQGRVWSONWFJJD-UHFFFAOYSA-N 0.000 description 2
IBZKBSXREAQDTO-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)ethanamine Chemical compound COCCNCCOC IBZKBSXREAQDTO-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PXALERQQASXBPS-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)OC(CCCC)=O Chemical compound COC1=C(C(=CC=C1)OC)OC(CCCC)=O PXALERQQASXBPS-UHFFFAOYSA-N 0.000 description 2
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102000027484 GABAA receptors Human genes 0.000 description 2
108091008681 GABAA receptors Proteins 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000003444 anaesthetic effect Effects 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000027455 binding Effects 0.000 description 2
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238000007911 parenteral administration Methods 0.000 description 2
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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AZORXPWSCIGVTE-UHFFFAOYSA-N (2,6-dimethoxy-4-methylphenyl) 2-bromo-3-methylbutanoate Chemical compound COC1=CC(C)=CC(OC)=C1OC(=O)C(Br)C(C)C AZORXPWSCIGVTE-UHFFFAOYSA-N 0.000 description 1
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BOIAKKNKVBLOTH-UHFFFAOYSA-N (2,6-dimethoxy-4-methylphenyl) 2-bromopropanoate Chemical compound COC1=CC(C)=CC(OC)=C1OC(=O)C(C)Br BOIAKKNKVBLOTH-UHFFFAOYSA-N 0.000 description 1
YXKGAPMZAGMSGB-UHFFFAOYSA-N (2,6-dimethoxy-4-methylphenyl) pentanoate Chemical compound COC1=C(C(=CC(=C1)C)OC)OC(CCCC)=O YXKGAPMZAGMSGB-UHFFFAOYSA-N 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
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- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
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- C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
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Psychiatry (AREA)
Anesthesiology (AREA)
Rheumatology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK103-2001A 1998-07-22 1999-07-16 Alpha-amino acid phenyl ester derivatives SK1032001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP98305837		1998-07-22
PCT/EP1999/005051 WO2000005196A1 (en)	1998-07-22	1999-07-16	α-AMINO ACID PHENYL ESTER DERIVATIVES

Publications (1)

Publication Number	Publication Date
SK1032001A3 true SK1032001A3 (en)	2001-08-06

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ID=8234960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK103-2001A SK1032001A3 (en)	1998-07-22	1999-07-16	Alpha-amino acid phenyl ester derivatives

Country Status (27)

Country	Link
US (1)	US6451854B1 (de)
EP (1)	EP1098871B1 (de)
JP (1)	JP2002521358A (de)
KR (1)	KR100599142B1 (de)
CN (1)	CN1183101C (de)
AR (1)	AR021165A1 (de)
AT (1)	ATE244697T1 (de)
AU (1)	AU758808B2 (de)
BR (1)	BR9912291A (de)
CA (1)	CA2337945A1 (de)
CO (1)	CO5080742A1 (de)
DE (1)	DE69909486T2 (de)
DK (1)	DK1098871T3 (de)
ES (1)	ES2203163T3 (de)
HU (1)	HUP0102705A3 (de)
ID (1)	ID27261A (de)
IL (1)	IL140586A (de)
NO (1)	NO20010280L (de)
NZ (1)	NZ509327A (de)
PE (1)	PE20000880A1 (de)
PL (1)	PL345621A1 (de)
PT (1)	PT1098871E (de)
RU (1)	RU2223947C2 (de)
SK (1)	SK1032001A3 (de)
TR (1)	TR200100166T2 (de)
TW (1)	TW565546B (de)
WO (1)	WO2000005196A1 (de)

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Publication number	Priority date	Publication date	Assignee	Title
AR031473A1 (es) *	2000-11-20	2003-09-24	Lundbeck & Co As H	Intensificadores de gaba en el tratamiento de enfermedades relacionadas con una reducida actividad neuroesteroide
JP4043363B2 (ja) *	2001-01-19	2008-02-06	ナームローゼ・フエンノートチヤツプ・オルガノン	催眠薬としてのアラニン２，６−ジアルコキシフェニルエステル誘導体
CN120965524B (zh) *	2025-10-21	2026-01-09	四川大学	一种(n,n-二甲基氨基)甲酸-4,5-二甲氧基-2-[(1e)-3-甲氧基-丙烯基]苯基酯化合物及其制备方法和应用

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GB1102011A (en) *	1964-05-21	1968-02-07	Richardson Merrell Spa	Phenol esters of amino acids
GB1160468A (en)	1967-05-08	1969-08-06	May & Baker Ltd	Morpholine Derivative
SU495828A3 (ru) *	1972-10-12	1975-12-15	Ф.Гоффманн-Ля Рош И Ко Аг. (Фирма)	Способ получени мета-производных бензойной кислоты

1999
- 1999-07-16 DK DK99936544T patent/DK1098871T3/da active
- 1999-07-16 EP EP99936544A patent/EP1098871B1/de not_active Expired - Lifetime
- 1999-07-16 PT PT99936544T patent/PT1098871E/pt unknown
- 1999-07-16 ES ES99936544T patent/ES2203163T3/es not_active Expired - Lifetime
- 1999-07-16 JP JP2000561153A patent/JP2002521358A/ja active Pending
- 1999-07-16 KR KR1020017000592A patent/KR100599142B1/ko not_active Expired - Fee Related
- 1999-07-16 CN CNB998091308A patent/CN1183101C/zh not_active Expired - Fee Related
- 1999-07-16 AT AT99936544T patent/ATE244697T1/de not_active IP Right Cessation
- 1999-07-16 NZ NZ509327A patent/NZ509327A/xx unknown
- 1999-07-16 RU RU2001104896/04A patent/RU2223947C2/ru not_active IP Right Cessation
- 1999-07-16 WO PCT/EP1999/005051 patent/WO2000005196A1/en not_active Ceased
- 1999-07-16 TR TR2001/00166T patent/TR200100166T2/xx unknown
- 1999-07-16 DE DE69909486T patent/DE69909486T2/de not_active Expired - Fee Related
- 1999-07-16 PL PL99345621A patent/PL345621A1/xx not_active IP Right Cessation
- 1999-07-16 BR BR9912291-0A patent/BR9912291A/pt not_active Application Discontinuation
- 1999-07-16 HU HU0102705A patent/HUP0102705A3/hu unknown
- 1999-07-16 IL IL14058699A patent/IL140586A/en not_active IP Right Cessation
- 1999-07-16 AU AU51602/99A patent/AU758808B2/en not_active Ceased
- 1999-07-16 ID IDW20010160A patent/ID27261A/id unknown
- 1999-07-16 CA CA002337945A patent/CA2337945A1/en not_active Abandoned
- 1999-07-16 SK SK103-2001A patent/SK1032001A3/sk unknown
- 1999-07-16 US US09/744,004 patent/US6451854B1/en not_active Expired - Fee Related
- 1999-07-21 CO CO99045953A patent/CO5080742A1/es unknown
- 1999-07-21 PE PE1999000731A patent/PE20000880A1/es not_active Application Discontinuation
- 1999-07-21 AR ARP990103567A patent/AR021165A1/es active IP Right Grant
- 1999-07-23 TW TW088112565A patent/TW565546B/zh not_active IP Right Cessation
2001
- 2001-01-17 NO NO20010280A patent/NO20010280L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
TR200100166T2 (tr)	2001-05-21
WO2000005196A1 (en)	2000-02-03
PT1098871E (pt)	2003-11-28
ID27261A (id)	2001-03-22
KR100599142B1 (ko)	2006-07-12
ATE244697T1 (de)	2003-07-15
RU2223947C2 (ru)	2004-02-20
DK1098871T3 (da)	2003-10-27
HUP0102705A3 (en)	2002-11-28
DE69909486D1 (de)	2003-08-14
CN1311770A (zh)	2001-09-05
CN1183101C (zh)	2005-01-05
HUP0102705A2 (hu)	2001-12-28
NZ509327A (en)	2003-04-29
TW565546B (en)	2003-12-11
PE20000880A1 (es)	2000-09-12
CO5080742A1 (es)	2001-09-25
EP1098871A1 (de)	2001-05-16
CA2337945A1 (en)	2000-02-03
AU5160299A (en)	2000-02-14
JP2002521358A (ja)	2002-07-16
KR20010071905A (ko)	2001-07-31
PL345621A1 (en)	2002-01-02
NO20010280L (no)	2001-03-08
ES2203163T3 (es)	2004-04-01
NO20010280D0 (no)	2001-01-17
EP1098871B1 (de)	2003-07-09
IL140586A0 (en)	2002-02-10
BR9912291A (pt)	2001-04-17
US6451854B1 (en)	2002-09-17
IL140586A (en)	2004-06-01
DE69909486T2 (de)	2004-05-27
AR021165A1 (es)	2002-07-03
AU758808B2 (en)	2003-03-27

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